Affectionately nicknamed 'King Richard' because of his exploits on the field, Reynolds played 320 games and kicked 442 goals in a 19 season career with Essendon (1933 - 1951). He won three Brownlow medals in five years (1934 at the age of 19, he was the youngest player to win the coveted award, 1937 and 1938), and seven best and fairest awards (1934, 1936, 1937, 1938, 1939, 1942 and 1943).

As well as playing for the Bombers, Reynolds also took over the coaching role midway through the 1939 season, and remained in charge until 1960, even after his playing career had come to an end in 1951. He played on the wing, centre half forward, but his preferred position was rover.

Reynolds was captain-coach from 1939 at the age of 24, until 1950 and upon retiring after the grand final, he returned at the age of 36 for the 1951 grand final, losing against Geelong. He coached from 1951 to 1960, coaching a total of 415 games. He played in ten grand finals and captain-coached the Dons to four premierships, in 1942, 1946, 1949 and 1950, played 19 times for Victoria, including six as captain, and also coached the state team in 1959. He was a member of the Victorian Carnival side of 1937.

In 1961, he joined South Australian club West Torrens, coaching them from 1961 to 1963.